(R)-2-(isopropylamino)-1-(naphthalen-2-yl)ethanol | 5696-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(isopropylamino)-1-(naphthalen-2-yl)ethanol
• 英文别名: 2-(isopropylamino)-1-(2-naphthyl)ethanol；(R)-(-)-Pronethalol；(R)-pronethalol；(R)-2-(N-isopropylamino)-1-(2-naphthyl)ethanol；(R)-2-Isopropylamino-1-(2-naphthyl)-ethanol；(1R)-1-naphthalen-2-yl-2-(propan-2-ylamino)ethanol
• CAS: 5696-91-3
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: HRSANNODOVBCST-HNNXBMFYSA-N

物化性质

• 沸点：
  322.4±9.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 甲醇 、 MP-TsOH 作用下， 以91%的产率得到(R)-2-(isopropylamino)-1-(naphthalen-2-yl)ethanol
  参考文献：
  名称：

  Short asymmetric syntheses of bioactive β-aryl ethanolamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition

  摘要：

  Short, stereoselective and efficient total syntheses of the bioactive beta-aryl ethanolamine derivatives (R)-tembamide, (R)-aegeline and (R)-pronethalol have been achieved using the highly diastereoselective oxy-Michael addition of 'naked' delta lactol anions to nitro olefins as the key step. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.018

文献信息

• Minor Enantiomer Recycling: Application to Enantioselective Syntheses of Beta Blockers
  作者：Ye-Qian Wen、Robin Hertzberg、Inanllely Gonzalez、Christina Moberg

  DOI：10.1002/chem.201303890

  日期：2014.3.24

  Continuous recycling of the minor product enantiomer obtained from the acetylcyanation of prochiral aldehydes provided access to highly enantiomerically enriched products. Cyanohydrin derivatives, which under normal conditions are obtained with modest or poor enantiomeric ratios, were formed with high enantiomeric purity by using a reinforcing combination of a chiral Lewis acid catalyst and a biocatalyst

  从手性醛的乙酰氰化获得的次要产物对映异构体的连续再循环提供了高度对映异构体富集的产物的获得。通过使用手性路易斯酸催化剂和生物催化剂的增强组合，以高对映体纯度形成在正常条件下以适中或较差的对映体比例获得的氰醇衍生物。通过两步程序，将最初获得的产物转化为β-肾上腺素能拮抗剂（S）-丙醇，（R）-二氯异丙基肾上腺素和（R）-nethalalol。
• One-pot route to β-adrenergic blockers via enantioselective organocatalysed epoxidation of terminal alkenes as a key step
  作者：Felix E. Held、Shengwei Wei、Kathrin Eder、Svetlana B. Tsogoeva

  DOI：10.1039/c4ra04011b

  日期：——

  A convenient and environmentally attractive one-pot two-step process for the synthesis of β-adrenergic blockers via Shi's organocatalytic epoxidation of terminal alkenes and subsequent aminolysis reaction of epoxides with isopropylamine under mild reaction conditions has been developed.

  开发了一种方便且环境友好的两步一锅法合成β-肾上腺素阻断剂的过程，该过程通过Shi的末端烯烃有机催化环氧化反应，随后在温和反应条件下利用异丙胺进行环氧化物的氨基解反应实现。
• Asymmetric Synthesis of β-Adrenergic Blockers through Multistep One-Pot Transformations Involving In Situ Chiral Organocatalyst Formation
  作者：Shengwei Wei、Regina Messerer、Svetlana B. Tsogoeva

  DOI：10.1002/chem.201102931

  日期：2011.12.16

  Two birds one stone: A new atom‐economical one‐pot approach to enantioselective chiral drug synthesis, involving in situ multistep organocatalyst formation and the application of the reaction for multistep sequential synthesis of β‐adrenergic blockers is disclosed (see scheme).

  两只鸟一块石头：公开了一种用于对映选择性手性药物合成的新的原子经济单罐方法，该方法涉及原位多步有机催化剂的形成以及该反应在β-肾上腺素能阻滞剂多步序贯合成中的应用（参见方案）。
• One-Pot Cascade Hydration-Asymmetric Transfer Hydrogenation as a Practical Strategy to Construct Chiral β-Adrenergic Receptor Blockers
  作者：Qunqun Ye、Tanyu Cheng、Yuxi Zhao、Junwei Zhao、Ronghua Jin、Guohua Liu

  DOI：10.1002/cctc.201500409

  日期：2015.6.15

  the Au‐catalyzed hydration of aryl‐substituted haloalkynes to aryl‐substituted α‐halomethyl ketones and the Ru‐catalyzed asymmetric transfer hydrogenation of aryl‐substituted α‐halomethyl ketones to aryl‐substituted 2‐haloethanols. The significant benefits of this procedure are that it provides chiral aromatic halohydrins in high yields, with excellent enantioselectivities, and a wide variety of functional

  具有生物活性的β-肾上腺素能受体激动剂/阻滞剂和类似物的简便构建是医学化学中一项重大的基础性和实践性挑战。本文中，我们报道了一种水合-不对称转移氢化级联反应，可实现芳族卤代炔烃向手性芳族卤代醇的单锅对映选择性转化，该手性芳族卤代醇可轻松转化为手性β-肾上腺素能受体阻滞剂。这样的一锅级联过程涉及芳基取代的卤代炔烃的金催化水合为芳基取代的α-卤代甲基酮，以及Ru催化的芳基取代的α-卤代甲基酮的不对称转移加氢为芳基取代的2-卤代乙醇。该方法的显着优点是，它可提供高收率的手性芳族卤代醇，并且具有出色的对映选择性，在温和条件下可以耐受各种官能团。本文所述研究为构建手性β-肾上腺素能阻滞剂提供了一种有用的方法，这是一种有吸引力的实用有机转化方法，可单锅法进行。
• Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines
  作者：WR Jackson、HA Jacobs、GS Jayatilake、BR Matthews、KG Watson

  DOI：10.1071/ch9902045

  日期：——

  Cyanohydrins, prepared in high optical purity from aryl aldehydes, have been converted into α- hydroxy aldehydes, β- hydroxy ketones and β- hydroxy amines without any racemization and frequently with good stereoselectivity for the erythro-diastereoisomer (>90%) at the newly introduced stereogenic centre.

  从芳基醛中制备的高光学纯度氰基卤素可转化为 α-羟基醛、β-羟基酮和β-羟基胺，且无任何外消旋化现象，在新引入的立体中心处，赤式二对映异构体通常具有良好的立体选择性（90%）。